4-cyano-N-(3-bromophenyl)thiazole-2-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-cyano-N-(3-bromophenyl)thiazole-2-carboxamide
• 英文别名: N-(3-bromophenyl)-4-cyano-1,3-thiazole-2-carboxamide
• 化学式: C₁₁H₆BrN₃OS
• 分子量: 308.158
• InChiKey: CVVPHCMIATWDGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 4-cyanothiazole-2-carboxylate 在 N-甲基吗啉 、 sodium tetrahydroborate 、 重铬酸吡啶 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4-cyano-N-(3-bromophenyl)thiazole-2-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of picolinamides and thiazole-2-carboxamides as mGluR5 (metabotropic glutamate receptor 5) antagonists

  摘要：

  We described here the synthesis and biological evaluation of picolinamides and thiazole-2-carboxamides as potential mGluR5 antagonists. We found that a series of thiazole derivatives 6 showed better inhibitory activity against mGluR5. Compounds 6bc and 6bj have been identified as potent antagonists (IC50 = 274 and 159 nM) showing excellent in vitro stability profile. Molecular docking study using the crystal structure of mGluR5 revealed that our compounds 6bc and 6bj fit the allosteric binding site of mavoglurant well. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.012

文献信息

• Synthesis and biological evaluation of picolinamides and thiazole-2-carboxamides as mGluR5 (metabotropic glutamate receptor 5) antagonists
  作者：Hoang Nam Vu、Ji Young Kim、Ahmed H.E. Hassan、Kihang Choi、Jong-Hyun Park、Ki Duk Park、Jae Kyun Lee、Ae Nim Pae、Hyunah Choo、Sun-Joon Min、Yong Seo Cho

  DOI：10.1016/j.bmcl.2015.11.012

  日期：2016.1

  We described here the synthesis and biological evaluation of picolinamides and thiazole-2-carboxamides as potential mGluR5 antagonists. We found that a series of thiazole derivatives 6 showed better inhibitory activity against mGluR5. Compounds 6bc and 6bj have been identified as potent antagonists (IC50 = 274 and 159 nM) showing excellent in vitro stability profile. Molecular docking study using the crystal structure of mGluR5 revealed that our compounds 6bc and 6bj fit the allosteric binding site of mavoglurant well. (C) 2015 Elsevier Ltd. All rights reserved.